Cruise and Beach Destinations
in the Caribbean, Mexico & Beyond

3 Great Caribbean Family Vacations

Western Caribbean cruises are popular partly because of Stingray City. Credit: Pixabay license

The best Caribbean family vacation usually comes down to three basic choices – a cruise, an all-inclusive resort or a hotel with great tourist attractions nearby.

Family vacations in the Caribbean also have other factors that make them good and sometimes bad choices.

Some islands have more educational opportunities than others, some allow topless sunbathing while others forbid it and some are more or less likely to have crowds of college students during spring break.

People have different opinions about the best vacations. Our picks are based on more than 20 trips to the Caribbean including multiple cruises that took us to every major island.

1. Cruises

Western Caribbean

Our favorite Caribbean family vacation was a western Caribbean cruise that embarked from San Juan and went to Jamaica, Grand Cayman and Cozumel. San Juan has one of the best historical and shopping districts in the Caribbean at Old San Juan.

The best family excursions on the trip were Dunn’s River Falls near Ocho Rios, Jamaica, and Stingray City in Grand Cayman. Runner up: Cave tubing in Belize on another western Caribbean cruise. Attractions of ports on the Central America coast, especially Belize and Costa Rica, are big on ecotourism and Mayan ruins.

For families on a tight budget, any Caribbean cruise will provide the most value for the least amount of money.

Eastern Caribbean

An eastern Caribbean cruise is just as inexpensive on a per night, per cabin basis as a western cruise.

The excursions are good, but not at the same level as Old San Juan, Dunn’s River Falls, Belize cave tubing and Stingray City. But it does have better ports of call with great shopping and dining districts. They include Charlotte Amalie in St. Thomas, Philipsburg in St. Maarten, St. Johns in Antigua and Nassau in the Bahamas.

June is one of the best times to go on an eastern cruise for warm weather and low risk of rain. The risk of rain increases into the summer and fall.

2 - All-Inclusive Resorts

Dominican Republic

All inclusive resorts in Dominican Republic, which is one of the most popular Caribbean destinations, deserve a solid second place. The resorts in Punta Cana and Puerto Plata are large and filled with a massive number of things to do on the resort properties.

Children will enjoy the freedom of grabbing food whenever they want, playing in elaborate garden pools and swimming in the aqua waters off powdery, white-sand beaches. Parents will appreciate the security fences that surround the resort, the guards who stroll nearby and the ability of resort activities to keep their kids busy enough while the parents relax.

The biggest downside to all-inclusive resorts is the price. They are usually the most expensive option of any Caribbean family vacation.

3 - Hotel Destinations


Cancun has several advantages as a family vacation. It is closer to the U.S. and Canada than most Caribbean destinations, so flights are plentiful and cheaper. For first time visitors to the Caribbean, Cancun is an easy choice because it is more commercial and developed. The hotels and resorts are large and luxurious. Chichen Itza is one of the most educational excursions in the Caribbean.

The tourist area also has an inexpensive public bus system that runs visitors from their hotels to the various restaurants and shopping centers that line the strip. And the strip itself is long and narrow, making everything easy to find.


Convenience makes Aruba a safe choice. © Aruba Tourism Authority

Aruba may surprise some people as the No. 5 on the list, but it’s here because everything on the island is nearby, convenient and easy for parents to manage.

For U.S., Canada and United Kingdom visitors, English is widely spoken. A public bus system makes it easy to travel between hotels and the nearby capital city of Oranjestad. Palm Beach has one of the best beaches in the Caribbean and one of the best shopping and dining districts (especially at night).

The island, which claims the highest visitor return rate in the region, does not have any major family excursions such as Stingray City. But it is known for snorkeling, scuba diving and many shipwrecks along with kite surfing, wind surfing and various land activities. Average rainfall is the lowest in the Caribbean.

The biggest downside is the distance—it is located in the southern Caribbean off the coast of Venezuela. Flights are longer and more expensive than more northern destinations such as Cancun.

Tips for Choosing Best Family Islands

Families with children in their mid-teens or older might find an all-inclusive resort or a hotel at a destination with nearby activities the better choice.

An all-inclusive resort will have many of the same activities as a cruise, but these large properties on sometimes hundreds of acres of land – and usually surrounded by tall security fencing – allow teens a greater degree of quiet and freedom than on a typical cruise ship.

Major destinations that emphasize all-inclusive resorts include Jamaica and Dominican Republic. However, most major resort locations for Jamaica and Dominican Republic have few things to do outside of the resort property.

Other destinations with fewer resorts, more hotels and more things to do nearby include Aruba, Cancun (which is popular during spring break), Bahamas and the Virgin Islands.

It is important for some families to know that topless sunbathing is often allowed at destinations with a French, Dutch or Spanish heritage while those with a British heritage don’t allow it.

Topless sunbathing is more common at places such as Martinique, St. Maarten and Guadeloupe and to a lesser extent at Aruba and Dominican Republic.

It is usually forbidden at Antigua, Bahamas, Barbados, Bermuda, Cayman Islands, Dominica, St. Kitts, St. Lucia, Trinidad, Turks and Caicos, and the Virgin Islands.

Tips for Choosing Best Family Cruises

Caribbean cruise vacations appeal to families with younger kids and those in their early teens because of the activities, the food and the freedom that the kids experience.

On-board activities typically include indoor and outdoor events scheduled throughout the day; programs specifically for younger kids and teens; and nighttime shows with dancers, singers and other entertainers.

More standard things to do are based on ship facilities. A swimming pool, spa, fitness center, casino, lounges and shopping mall are common with most major cruise ships.

Some ships also offer nightclubs with scheduled times – usually in the late afternoon to early evening – for both younger kids and teens in addition to adults.

Depending on the ship, other facilities may include tennis courts, basketball courts, water slides, climbing walls, jogging tracks and even nine-hole golf courses.

But some of the best Caribbean family vacation experiences on a cruise ship take place at shore-side excursions.

A seven-day cruise typically will visit about four or five destinations. Most of these destinations have cultural, historical and natural attractions. But they also have at least one or two noteworthy excursions, such as swimming with dolphins, sting rays or sea turtles.

Although these excursions cost extra, they usually are the most memorable experiences on any Caribbean family vacation.